(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

Base Information

Chemical Name:(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde
CAS No.:676126-64-0
Molecular Formula:C₂₂H₂₆O₇
Molecular Weight:402.444
Hs Code.:

Synonyms:(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

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Chemical Property of (2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

Chemical Property:

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Technology Process of (2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

There total 12 articles about (2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 115693-78-2,142226-15-1,69940-02-9
1,2:5,6-di-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 676126-64-0
(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1.1: 82 percent / aq. AcOH / 24 h / 20 °C

2.1: aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

2.2: 87 percent / aq. NaOH / dioxane / 24 h / 20 °C

3.1: 93 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 83 percent / aq. HCl / 36 h / 20 °C

5.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

6.1: 18-crown-6-ether / CH₂Cl₂; toluene / 12 h / 50 °C

7.1: ammonia / methanol / 24 h / 20 °C

7.2: NaH / dimethylformamide / 12 h / 20 °C

8.1: 18-crown-6 / dioxane / 12 h / Heating

9.1: ammonia / methanol / 12 h / 20 °C

10.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

10.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

11.1: aq. AcOH / 12 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; 18-crown-6 ether; ammonia; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 2.2: Cannizzaro reaction;
DOI:10.1039/b310719a

Reference yield:

: 109536-51-8,142226-16-2,69940-04-1
1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 676126-64-0
(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1.1: aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

1.2: 87 percent / aq. NaOH / dioxane / 24 h / 20 °C

2.1: 93 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

3.1: 83 percent / aq. HCl / 36 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

5.1: 18-crown-6-ether / CH₂Cl₂; toluene / 12 h / 50 °C

6.1: ammonia / methanol / 24 h / 20 °C

6.2: NaH / dimethylformamide / 12 h / 20 °C

7.1: 18-crown-6 / dioxane / 12 h / Heating

8.1: ammonia / methanol / 12 h / 20 °C

9.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

9.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

10.1: aq. AcOH / 12 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; 18-crown-6 ether; ammonia; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 1.2: Cannizzaro reaction;
DOI:10.1039/b310719a

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 676126-64-0
(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

1.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

2.1: 82 percent / aq. AcOH / 24 h / 20 °C

3.1: aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

3.2: 87 percent / aq. NaOH / dioxane / 24 h / 20 °C

4.1: 93 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

5.1: 83 percent / aq. HCl / 36 h / 20 °C

6.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

7.1: 18-crown-6-ether / CH₂Cl₂; toluene / 12 h / 50 °C

8.1: ammonia / methanol / 24 h / 20 °C

8.2: NaH / dimethylformamide / 12 h / 20 °C

9.1: 18-crown-6 / dioxane / 12 h / Heating

10.1: ammonia / methanol / 12 h / 20 °C

11.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

11.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

12.1: aq. AcOH / 12 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; 18-crown-6 ether; ammonia; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 3.2: Cannizzaro reaction;
DOI:10.1039/b310719a